Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester | 852371-69-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester
• CAS: 852371-69-8
• 化学式: C₃₃H₄₃N₃O₇SSi
• 分子量: 653.872
• InChiKey: YYOWWZPONRXNIP-ROQXEPJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  45.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  129.05
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester 在 lithium hydroxide 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 四丁基氟化铵 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 (1S,2R,3S,4S,5R,6S)-3-((2S,3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-yloxy)-4,5,6-tris-benzyloxy-cyclohexane-1,2-diol
  参考文献：
  名称：

  A fluorescent inositol phosphate glycan stimulates lipogenesis in rat adipocytes by extracellular activation alone

  摘要：

  The chemical synthesis of 2,6-dideoxy-2-amino-6-mercaptoglucopyranosyl-(alpha 1-6)-myo-inositol 1,2-cyclic phosphate and its conjugation with a lucifer yellow derivative are reported. The resulting fluorescent IPG analogue was able to stimulate lipogenesis in rat adipocytes despite the fact that it was not internalized into the cell. The results demonstrate that internalization of the IPG is not required for manifestation of its insulin-like effects. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.061
• 作为产物：
  描述：

  tert-butyldimethylsilyl 2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside 、 对甲苯磺酰氯 在 吡啶 作用下， 以89%的产率得到Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  A fluorescent inositol phosphate glycan stimulates lipogenesis in rat adipocytes by extracellular activation alone

  摘要：

  The chemical synthesis of 2,6-dideoxy-2-amino-6-mercaptoglucopyranosyl-(alpha 1-6)-myo-inositol 1,2-cyclic phosphate and its conjugation with a lucifer yellow derivative are reported. The resulting fluorescent IPG analogue was able to stimulate lipogenesis in rat adipocytes despite the fact that it was not internalized into the cell. The results demonstrate that internalization of the IPG is not required for manifestation of its insulin-like effects. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.061